The ability to silylate organic moieties has attracted significant attention in recent years, owing to the utility of the silylated materials in their own rights and as intermediates for other important materials used, for example, in agrichemical, pharmaceutical, and electronic material applications.
Over the past several decades, considerable effort has been allocated to the development of powerful catalyst architectures to accomplish a variety of C—H functionalization reactions, revolutionizing the logic of chemical synthesis and consequently streamlining synthetic chemistry. Accomplishing such challenging transformations can often necessitate the use of stoichiometric additives, demanding reaction conditions, complex ligands, and most notably precious metal catalysts. The need to use precious metal catalysts for these transformations remains a fundamental and longstanding limitation.
Strategies for the synthesis of vinylsilanes and allylsilanes have employed strong bases or have relied on stoichiometric or catalytic transition metal species such as Au, Co, Cr, Cu, Ir, Fe, Os, Ni, Pd, Pt, Rh, Ru, Ti, and Zn, typically using various alkyne starting materials (i.e., hydrosilylation reactions) and/or halogenated silylating reagents. These factors have led to important limitations in scope and practical utility. For example, in certain applications such as electronics, the presence of residual metals can adversely affect performance. In pharmaceuticals, the presence of residual metals is strictly regulated. The development of a mild and general stoichiometric or catalytic method for cross-dehydrogenative C(sp2)-Si bond formation from C—H bonds remains a longstanding challenge in the field.
The present invention takes advantage of the discoveries cited herein to avoid at least some of the problems associated with previously known methods.